Weren't we talking about the near future, starting from where both clubs are now? So I'm not sure why you hark back to the last 15 or 16 years ... but the fact that you have does tie in with what I said about Liverpool FC being still not fully adjusted to being seen as 2nd tier and thus falling between two stools. And you didn't respond to what I've said about player recruitment and "unearthing" gems.
You mention a massive cash injection, but that is precisely what Spurs will be getting in due course from our new stadium complex (note: not just a new football stadium). A lot of people still haven't understood the full scale of what's involved in this project and are thinking only in terms of extra income from ticket sales to Spurs matches and corporate boxes, even though this increase alone will be substantial. For such folk I'd recommend they take a look:
http://www.tottenhamhotspur.com/new-scheme/
So yes, considering that Spurs have finished top 4 twice in recent seasons and often 5th or thereabouts otherwise with our current income, I'm confident that after the new stadium complex is finished we'll become regular top 4 finishers.
As for Harry Kane, he'll still be at Spurs next season. I'm willing to bet on it.
Thanks for Liverpool stadium update.